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Product Details of [ 4102-60-7 ]

CAS No. :4102-60-7 MDL No. :MFCD00034591
Formula : C18H33Br Boiling Point : -
Linear Structure Formula :- InChI Key :SBRPUFDSMGABKD-AVQMFFATSA-N
M.W : 329.36 Pubchem ID :6001965
Synonyms :

Calculated chemistry of [ 4102-60-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 14
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 95.56
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -2.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.85
Log Po/w (XLOGP3) : 8.69
Log Po/w (WLOGP) : 7.19
Log Po/w (MLOGP) : 6.1
Log Po/w (SILICOS-IT) : 7.33
Consensus Log Po/w : 6.83

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.43
Solubility : 0.000122 mg/ml ; 0.000000369 mol/l
Class : Poorly soluble
Log S (Ali) : -8.57
Solubility : 0.000000889 mg/ml ; 0.0000000027 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -6.54
Solubility : 0.0000961 mg/ml ; 0.000000292 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.1

Safety of [ 4102-60-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4102-60-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 4102-60-7 ]
  • Downstream synthetic route of [ 4102-60-7 ]

[ 4102-60-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 51154-39-3 ]
  • [ 4102-60-7 ]
YieldReaction ConditionsOperation in experiment
100% With magnesium bromide ethyl etherate In diethyl ether for 21 h; Inert atmosphere Synthesis of Linoleyl Bromide (II)A mixture of linoleyl methane sulfonate (6.2g, 18 mmol) and magnesium bromide etherate (17g, 55 mmol) in anhydrous ether (300 mL) was stirred under argon overnight (21 hours). The resulting suspension was poured into 300 mL of chilled water. Upon shaking, the organic phase was separated. The aqueous phase was extracted with ether (2 x 150 mL). The combined ether phase was washed with water (2 x 150 mL), brine (150 mL), and dried over anhydrous Na2SO4. The solvent was evaporated to afford 6.5g of colourless oil. The crude product was purified by column chromatography on silica gel (230- 400 mesh, 300 mL) and eluted with hexanes. This gave 6.2 g (approximately 100percent) of linoleyl bromide (II). 1 H NMR (400 MHz, CDCI3) δ: 5.27-5.45 (4H, m, 2 x CH=CH), 3.42 (2H, t, CH2Br), 2.79 (2H, t, C=C-CH2-C=C), 2.06 (4H, q, 2 x allylic CH2), 1.87 (2H, quintet, CH2), 1.2-1.5 (16H, m), 0.90 (3H, t, CH3) ppm.
100% With magnesium bromide ethyl etherate In diethyl ether for 21 h; Inert atmosphere A mixture of linoleyl methane sulfonate (6.2 g, 18 mmol) and magnesium bromide etherate (17 g, 55 mmol) in anhydrous ether (300 mL) was stirred under argon overnight (21 hours). The resulting suspension was poured into 300 mL of chilled water. Upon shaking, the organic phase was separated. The aqueous phase was extracted with ether (2.x.150 mL). The combined ether phase was washed with water (2.x.150 mL), brine (150 mL), and dried over anhydrous Na2SO4. The solvent was evaporated to afford 6.5 g of colourless oil. The crude product was purified by column chromatography on silica gel (230-400 mesh, 300 mL) eluted with hexanes. This gave 6.2 g (approximately 100percent) of linoleyl bromide (II). 1H NMR (400 MHz, CDCl3) : 5.27-5.45 (4H, m, 2.x.CHCH), 3.42 (2H, t, CH2Br), 2.79 (2H, t, CC-CH2-CC), 2.06 (4H, q, 2.x.allylic CH2), 1.87 (2H, quintet, CH2), 1.2-1.5 (16H, m), 0.90 (3H, t, CH3) ppm.
100% With magnesium bromide In diethyl ether for 21 h; Inert atmosphere [0204] A mixture of linoleyl methane sulfonate (6.2g, 18 mmol) and magnesium bromide etherate (17g, 55 mmol) inanhydrous ether (300 mL) was stirred under argon overnight (21 hours). The resulting suspension was poured into 300mL of chilled water. Upon shaking, the organic phase was separated. The aqueous phase was extracted with ether (2x 150 mL). The combined ether phase was washed with water (2 x 150 mL), brine (150 mL), and dried over anhydrous Na2SO4. The solvent was evaporated to afford 6.5g of colourless oil. The crude product was purified by column chromatographyon silica gel (230-400 mesh, 300 mL) eluted with hexanes. This gave 6.2 g (approximately 100percent) of linoleylbromide (II). 1 H NMR (400 MHz, CDCl3) δ: 5.27-5.45 (4H, m, 2 x CH=CH), 3.42 (2H, t, CH2Br), 2.79 (2H, t, C=CCH2-C=C), 2.06 (4H, q, 2 x allylic CH2), 1.87 (2H, quintet, CH2), 1.2-1.5 (16H, m), 0.90 (3H, t, CH3) ppm.
99% With magnesiumbromide etherate In diethyl etherInert atmosphere Magnesium bromide etherate (34 g, 1 10 mmol) and a stir bar were added to a 2000 mL round bottom flask. The flask was sealed and flushed with nitrogen.Anhydrous diethyl ether (400 mL) was added via canulla. A solution of linolenyl mesylate (20 g, 58 mmol) in anhydrous ether (300 mL) was then added, and the suspension stirred overnight. The suspension was poured into 500 mL of chilled water and transferred to a 2000-mL separating funnel. After shaking, the organic phase was separated. The aqueous phase was then extracted with ether (2 x 250 mL) and all ether phases combined. The ether phase was washed with water (2 x 250 mL), brine (250 mL) and dried over anhydrousMg2S04. The solution was filtered, concentrated and purified by flash chromatography. Final yield 18.9 g, 99percent.
99% With magnesium bromide ethyl etherate In diethyl etherInert atmosphere; Sealed tube General procedure: Step 1: Magnesium bromide etherate (34 g, 110 mmol) and a stir bar were added to a 2000 mL round bottom flask. The flask was sealed and flushed with nitrogen. Anhydrous diethyl ether (400 mL) was added via canulla. A solution of linolenyl mesylate (20 g, 58 mmol) in anhydrous ether (300 mL) was then added, and the suspension stirred overnight. The suspension was poured into 500 mL of chilled water and transferred to a 2000-mL separating funnel. After shaking, the organic phase was separated. The aqueous phase was then extracted with ether (2×250 mL) and all ether phases combined. The ether phase was washed with water (2×250 mL), brine (250 mL) and dried over anhydrous Mg2SO4. The solution was filtered, concentrated and purified by flash chromatography. Final yield 18.9 g, 99percent.
99% With magnesium bromide diethyl etherate In diethyl etherSealed tube; Inert atmosphere STEP 1: Magnesium bromide etherate (34 g, 110 mmol) and a stir bar were added to a 2000 mE round bottom flask. The flask was sealed and flushed with nitrogen. Anhydrous diethyl ether (400 mE) was added via canulla. A solution of linolenyl mesylate (20 g, 58 mmol) in anhydrous ether (300 mE) was then added, and the suspension stirred overnight. The suspension was poured into 500 mE of chilled water and transferred to a 2000-mE separating flannel. After shaking, the organic phase was separated. The aqueous phase was then extracted with ether (2x250 mE) and all ether phases combined. The ether phase was washed with water (2x250 mE), brine (250 mE) and dried over anhydrous Mg2SO4. The solution was filtered, concentrated and purified by flash chromatography. Final yield 18.9 g, 99percent.
97% With lithium bromide In diethyl ether at 20℃; for 24 h; Inert atmosphere Linoleyl methanesulfonate (27 g, 78 mmoles), anhydrous magnesium bromide (43 g; 238 mmoles), and 1000 ml of dry ether was placed in a 2500 ml three-necked flask equipped with reflux condenser, inlet and outlet tubes for dry nitrogen, and mechanical stirrer. The mixture was stirred vigorously at room temperature for 24 hr. More ether, and cold, degassed water were added after 24 hours. The water layer was extracted twice with ether. The combined ether phases were washed consecutively with water, 1percent potassium carbonate solution, and water, and are dried over anhydrous sodium sulfate. Concentration of the ether phase using a rotary evaporator yielded 25 g (97percent) of linoleyl bromide; mp −35° C.
94% With magnesium bromide ethyl etherate In diethyl ether for 26 h; Inert atmosphere; Reflux Synthesis of 18-Bromo-octadeca-6,9-diene 3
The mesylate 2 (13.44 g, 39 mmol) was dissolved in anhydrous ether (500 mL) and to it the MgBr.Et2O complex (30.7 g, 118 mmol) was added under argon and the mixture was refluxed under argon for 26 h after which the TLC showed the completion of the reaction.
The reaction mixture was diluted with ether (200 mL) and ice-cold water (200 mL) was added to this mixture and the layers were separated.
The organic layer was washed with 1percent aqueous K2CO3 (100 mL), brine (100 mL) and dried (Anhyd. Na2SO4).
Concentration of the organic layer provided the crude product which was further purified by column chromatography (silica gel) using 0-1percent Et2O in hexanes to isolate the bromide 3 (12.6 g, 94percent) as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ=5.41-5.29 (m, 4H), 4.20 (d, 2H), 3.40 (t, J=7 Hz, 2H), 2.77 (t, J=6.6 Hz, 2H), 2.09-2.02 (m, 4H), 1.88-1.00 (m, 2H), 1.46-1.27 (m, 18H), 0.88 (t, J=3.9 Hz, 3H). 13C NMR (CDCl3) δ=130.41, 130.25, 128.26, 128.12, 34.17, 33.05, 31.75, 29.82, 29.57, 29.54, 29.39, 28.95, 28.38, 27.42, 27.40, 25.84, 22.79, 14.28.
94% With magnesium bromide ethyl etherate In diethyl ether for 26 h; Inert atmosphere; Reflux The mesylate (2) (13.44 g, 39 mmol) was dissolved in anhydrous ether (500 mL) and to it the MgBr.Et2O complex (30.7 g, 118 mmol) was added under argon and the mixture was refluxed under argon for 26 h after which the TLC showed the completion of the reaction. The reaction mixture was diluted with ether (200 mL) and ice-cold 12 water (200 mL) was added to this mixture and the layers were separated. The organic layer was washed with 1percent aqueous K2CO3 (100 mL), brine (100 mL) and dried (Anhyd. Na2SO4). Concentration of the organic layer provided the crude product which was further purified by column chromatography (silica gel) using 0-1percent 9 Et2O in hexanes to isolate the bromide 3 (12.6 g, 94percent) as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ=5.41-5.29 (m, 4H), 4.20 (d, 2H), 3.40 (t, J=7 Hz, 2H), 2.77 (t, J=6.6 Hz, 2H), 2.09-2.02 (m, 4H), 1.88-1.00 (m, 2H), 1.46-1.27 (m, 18H), 0.88 (t, J=3.9 Hz, 3H). 13C NMR (CDCl3) δ=130.41, 130.25, 128.26, 128.12, 34.17, 33.05, 31.75, 29.82, 29.57, 29.54, 29.39, 28.95, 28.38, 27.42, 27.40, 25.84, 22.79, 14.28.
93% With magnesium bromide ethyl etherate In diethyl ether at 20℃; for 16 h; Step 2: (6Z,9Z)-18-Bro (3066) Chemical Formula: Ci8H33Br (3067) Molecular Weight: 329.37 (3068) [00836] To a solution of (9Z, 12Z)-octadeca-9, 12-dien-l-yl methanesulfonate (10.0 g, 29.0 mmol) in diethyl ether (372 mL) was added magnesium bromide ethyl etherate (22.5 g, 87.1 mmol). The reaction was let stir at room temperature for 16 hours. The mixture was quenched by the addition of water and extracted with diethyl ether. The combined organic layers were washed with 1percent K2CO3, brine, dried over anhydrous Na2SC>4, filtered, and concentrated in vacuo. Purification by ISCO silica flash chromatography provided (6Z,9Z)-18-bromooctadeca- 6,9-diene (8.9 g, 93percent). ^-NMR (300 MHz, CDC13) δ: ppm 5.36 (m, 4H); 3.41 (t, 2H); 2.77 (t, 2H); 2.05 (q, 4H); 1.86 (m, 2H); 1.48-1.22 (br. m, 16H); 0.89 (t, 3H).
92% With magnesium bromide ethyl etherate In diethyl ether at 20℃; for 2 h; Inert atmosphere To a solution of linoleyl methanesulfonate (26 g, 75 mmol) in ether (800 mL) was added magnesium bromide ethyl etherate (58.5 g, 226 mmol) under Argon. The reaction mixture was stirred at room temperature for 2 hrs. TLC was used to monitor reaction progress. If not completed, additional magnesium bromide ethyl etherate (14.5 g) was added the reaction mixture and the reaction mixture was stirred at room temperature for 22 hrs. TLC showed the reaction was complete (9/1 hexane/EtOAc). The reaction mixture was filtered, washed with ether (200 mL), hexane (100 mL), and concentrated under reduced pressure to give a residue, which was purified by ISCO (200 g gold silica gel cartridge) eluted with hexane to 10percent EtOAc in hexane to give linoleyl bromide (22.8 g, 69.2 mmol, 92 percent yield) as a colorless oil. 1H NMR (500 MHz, Chloroform-d) δ 5.42– 5.31 (m, 4H), 3.41 (t, J = 6.9 Hz, 2H), 2.77 (t, J = 6.6 Hz, 2H), 2.05 (q, J = 6.9 Hz, 4H), 1.85 (p, J = 6.9 Hz, 2H), 1.43– 1.25 (m, 16H), 0.89 (t, J = 6.8 Hz, 3H).
87% With magnesium bromide ethyl etherate In diethyl ether at 20℃; (9z,12z)-Octadecadien-1-methanesulfonate (10.64 g) was dissolved in diethyl ether (140 mL), magnesium bromide ethyl etherate (16.0 g, 61.8 mmol) was added to the solution, and the resulting mixture was stirred overnight at room temperature.
The reaction mixture was collected, and washed by using saturated aqueous sodium hydrogencarbonate (100 mL).
Then, anhydrous sodium sulfate was added to the organic layer for dehydration.
The organic layer was filtered, and the solvent was evaporated by using a rotating evaporator to obtain a crude product.
The crude product was purified by silica gel chromatography {elution solvent, hexane:ethyl acetate (continuous gradient) to obtain 18-bromo-octadeca-(6z,9z)-diene (8.85 g, 26.9 mmol) as colorless oil.
Yield was 87percent.
Proton nuclear magnetic resonance (1H NMR, 500 MHz) data of 18-bromo-octadeca-(6z,9z)-diene δ=0.88 (t, 3H), 1.27-1.46 (m, 18H), 1.80-1.88 (m, 2H), 2.00-2.09 (m, 4H), 2.77 (t, 2H), 3.40 (t, 2H), 4.20 (d, 2H), 5.29-5.41 (m, 4H)
81% With lithium bromide In N,N-dimethyl-formamide at -10 - 0℃; for 1.5 h; Inert atmosphere; Large scale A clean dry 200 L total glass reactor fitted with an argon inlet and a thermowell was charged with 25 L of DMF and 7.1 Kg of crude product from step 2. The mixture was cooled to -10 ° C. using an acetone-dry ice mixture. To this stirred mixture was added 25 L of a DMF solution of lithium bromide (2.7 Kg, 31.0 mol) over 1.5 hours while maintaining the reaction temperature below 0 ° C. After the addition was complete, the reaction mixture was stirred at 45 ° C. for 18-20 hours until TLC of the aliquot (10percent EtOAc in hexane, PMA staining) showed complete disappearance of the starting mesylate. The reaction mixture was diluted with 70 L of water and extracted with 57 L of hexane. The aqueous layer was further extracted with 2 × 10 L of hexane and the combined organic layers (~ 120 L was washed again with 2 × 10 L of water and 1 × 10 L of brine (prepared by dissolving 14 Kg of sodium chloride in 10 L of water) The resulting organic layer (120 L) was dried over sodium sulfate (4 Kg) and concentrated under reduced pressure to give a crude product (6.5 Kg) which was purified by elution with hexane And purified by column chromatography using 60-120 mesh silica gel.The concentration of the pure product gave 5.5 Kg (81percent, 3 steps) of bromide 4 as a colorless liquid.
45 g With magnesium bromide ethyl etherate In diethyl ether at 20℃; EXAMPLE 27 Synthesis of Cationic Lipid A [0372] Preparation of Intermediate A1: (6Z,9Z)-18-bromooctadeca-6,9-diene. [0373] In a 500 mL round-bottom flask equipped with a stir bar, Linoleyl Mesylate (50 g, 145 mmol) was dissolved in diethyl ether (200 mL). Magnesium bromide diethyl etherate (101 g, 392 mmol) was added slowly. Reaction was stirred overnight at room temperature. Brine and ether were added to the mixture in a separatory funnel. The organics were then washed with brine, dried over MgS04, filtered and concentrated under pressure to give crude product mixture. The crude was then purified by silica gel column chromatography eluting with 100percent heptane to afford 45 g product. 1H NMR (400 MHz, CDCI3) δ = 5.26 - 5.46 (m, 4 H) 3.42 (t, J=6.90 Hz, 2 H) 2.78 (t, J=6.65 Hz, 2 H) 2.06 (q, J=6.78 Hz, 4 H) 1.86 (dt, J=14.43, 7.09 Hz, 2 H) 1 .21 - 1.49 (m, 16 H) 0.82 - 0.95 (m, 3 H) ppm.
23 g With lithium bromide In N,N-dimethyl-formamide at -10 - 45℃; Inert atmosphere A 500 mL glass reactor fitted with an argon inlet was purged with dry argon, charged with 110 mL of DMF and 30 g (87 mmol) of product 3. This reaction mixture was cooled to −10° C. with acetone-dry-ice mixture. To the stirred reaction mixture, a LiBr solution (prepared by dissolving 11.5 g (132 mmol) LiBr in 110 mL of DMF) was added drop wise, while maintaining the reaction temperature below 0° C. After the completion of addition, the reaction mixture was heated to 45° C. and incubated for 18-20 hours under stirring. After the completion of reaction, 300 mL of water was added into the reaction mixture and the reaction mixture was extracted with 240 mL of n-hexane. The organic layers were combined, washed with 2×45 mL of brine solution (prepared by dissolving 59 g NaCl in 45 mL of water), and dried over Na2SO4 (17 g). The organic layer was filtered and condensed using a vacuum pump to remove the organic solvent, resulted in a crude product of 27.5 g. The crude product was purified by column chromatograph using 60-120 mesh silica gel (using n-hexanes as mobile phase), and resulted in 23 g of pure product 4 (the yield of the three steps is 81percent). 1H-NMR (CDCl3, 400 MHz), δ=5.41-5.29 (m, 4H), 4.20 (d, 2H), 3.40 (t, 2H), 2.77 (t, 2H), 2.09-2.02 (m, 4H), 1.88-1.00 (m, 2H), 1.46-1.27 (m, 18H), 0.88 (t, 3H).
5.5 kg With lithium bromide In N,N-dimethyl-formamide at -10 - 0℃; for 1.5 h; Inert atmosphere; Large scale A clean, dry 200 L all glass reactor fitted with argon inlet and thermowell was charged with 25 L of DMF and 7.1 Kg of the crude product from step 2. This mixture was cooled to −10° C. with acetone-dry-ice mixture. To this stirred mixture, a solution of lithium bromide (2.7 Kg, 31.0 mol) in 25 L of DMF was added over a period of 1.5 hrs while maintaining the reaction temperature below 0° C. After completion of the addition, the reaction mixture was stirred at 45° C. for 18-20 h until TLC (10percent EtOAc in hexanes, PMA stain) of an aliquot showed complete disappearance of the starting mesylate. The reaction mixture was diluted with 70 L of water and extracted with 57 L of hexanes. The aqueous layer was further extracted with 2×10 L of hexanes and the combined organic layers (approximately 120 L) were washed again with 2×10 L of water and 1×10 L of brine (prepared by dissolving 14 Kg of sodium chloride in 10 L of water). The obtained organic layer (120 L) was dried over sodium sulfate (4 Kg) and concentrated under reduced pressure to obtain the crude product (6.5 Kg). The crude product was purified by column chromatography using 60-120 mesh silica gel using hexanes as eluent. Concentration of the pure product provided 5.5 Kg (81percent, three steps) of the bromide 4 as a colorless liquid. 1H NMR (CDCl3, 400 MHz) δ=5.41-5.29 (m, 4H), 4.20 (d, 2H), 3.40 (t, J=7 Hz, 2H), 2.77 (t, J=6.6 Hz, 2H), 2.09-2.02 (m, 4H), 1.88-1.00 (m, 2H), 1.46-1.27 (m, 18H), 0.88 (t, J=3.9 Hz, 3H). 13C NMR (CDCl3) δ=130.41, 130.25, 128.26, 128.12, 34.17, 33.05, 31.75, 29.82, 29.57, 29.54, 29.39, 28.95, 28.38, 27.42, 27.40, 25.84, 22.79, 14.28.
22.8 g With magnesium bromide ethyl etherate In diethyl ether at 20℃; for 24 h; Inert atmosphere To a solution of linoleyl methanesulfonate (26 g, 75 mmol) in ether (800 mL) was added magnesium bromide ethyl etherate (58.5 g, 226 mmol) under Argon. The reaction mixture was stirred at room temperature for 2 hrs. TLC was used to monitor reaction progress. If not completed, additional magnesium bromide ethyl etherate (14.5 g) was added the reaction mixture and the reaction mixture was stirred at room temperature for 22 hrs. TLC showed the reaction was complete (9/1 hexane/EtOAc). The reaction mixture was filtered, washed with ether (200 mL), hexane (100 mL), and concentrated under reduced pressure to give a residue, which was purified by ISCO (200 g gold silica gel cartridge) eluted with hexane to 10percent EtOAc in hexane to give linoleyl bromide (22.8 g, 69.2 mmol, 92 percent yield) as a colorless oil. 1H NMR (500 MHz, Chloroform-d) 5 5.42 - 5.31 (m, 4H), 3.41 (t, J= 6.9 Hz, 2H), 2.77 (t,J= 6.6 Hz, 2H), 2.05 (q, J= 6.9 Hz, 4H), 1.85 (p, J= 6.9 Hz, 2H), 1.43 - 1.25 (m, 16H), 0.89 (t, J= 6.8 Hz, 3H).
23 g With lithium bromide In N,N-dimethyl-formamide at 0 - 45℃; 110ml DMF and 30g product 3 in the glass reactorCool to -10°C. 11.5g LiBr dissolved in 110ml DMF,Stir and slowly add dropwise to the reactorAnd keep the temperature of the reaction liquid below 0°C. After dropping,The reaction was warmed to 45°C and stirred overnight. After the reaction is completed,300 ml water was added and extracted with 240 ml n-hexane.The aqueous phase was further extracted with 2*45 ml of n-hexane. Combine the organic phase,It was washed with water and saturated brine and dried over sodium sulfate (17 g). filter,The organic phase was concentrated to remove the organic solvent to give 27.5 g of crude product.Purified with 60-120 mesh silica gel (n-hexane as the mobile phase),About 23 g of pure product 4 was obtained.
23 g With lithium bromide In N,N-dimethyl-formamide at -10 - 45℃; 110ml in glass reactor DMF and 30g products 3, Cool to -10 °C. 11.5 g of LiBr is dissolved in 110 ml of DMF. Stir and slowly add dropwise to the reactor, And keep the temperature of the reaction solution below 0 °C. After the addition is completed, The reaction solution was heated to 45 ° C. Stir overnight. After completion of the reaction, 300 ml of water was added and extracted with 240 ml of n-hexane, and the aqueous phase was further extracted with 2*45 ml of n-hexane. The combined organic layers were washed with water and aq.After filtration, the organic phase was concentrated to remove organic solvent to give a crude material (27.5 g). Purification with 60-120 mesh silica gel (n-hexane as mobile phase) gave about 23 g of pure product 4.

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  • 2
  • [ 506-43-4 ]
  • [ 4102-60-7 ]
YieldReaction ConditionsOperation in experiment
66% With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 20℃; To a solution of (9Z, 12Z)-octadeca-9, 12-dien- l -ol (5 g, 1 8.76 mmol) and PPh3 (5.22 g, 19.89 mmol) in DCM (60 mL) at 0 °C, was added NBS (3.87 g, 21 .77 mmol) in one portion. The reaction mixture was allowed to stir at 0 °C for 1 hour and then allowed to slowly warm to room temperature and allowed to stir for 1 hour. 240 mL of hexanes was added to the reaction mixture, filtered through a silica gel plug and concentrated in vacuo. 200 mL of hexanes was added to the reaction mixture, filtered through a silica gel plug and concentrated in vacuo to afford (6Z,9Z)-\ 8-bromooctadeca-6,9-diene (4.06 g, 12.33 mmol, 66percent). NMR (300 MHz, CDC13) δ: ppm 5.45-5.3 1 (br. m, 4H); 3.43 (t, 2H); 2.80 (m, 2H); 2.1 1 - 2.04 (br. m, 411); 1 .88 (m, 211); 1 .47-1 .33 (br. m, 1 H); 0.92 (m, 3H).
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 10, p. 1183 - 1190
[2] Patent: WO2017/99823, 2017, A1, . Location in patent: Page/Page column 337-338
[3] Journal of the Chemical Society, 1961, p. 3854 - 3858
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 34, p. 8529 - 8533
[5] Patent: US9120938, 2015, B2,
[6] Patent: US2015/272886, 2015, A1,
[7] Patent: US9186325, 2015, B2,
[8] Patent: US9394234, 2016, B2,
[9] Patent: JP2016/84297, 2016, A,
[10] Patent: WO2017/62862, 2017, A2,
[11] Patent: WO2017/112865, 2017, A1,
[12] Patent: US9701623, 2017, B2,
[13] Patent: US2017/273905, 2017, A1,
[14] Patent: WO2017/210647, 2017, A1,
[15] Patent: CN105085292, 2017, B,
[16] Patent: CN105085437, 2018, B,
  • 3
  • [ 60-33-3 ]
  • [ 4102-60-7 ]
Reference: [1] Patent: US2015/272886, 2015, A1,
[2] Patent: US9394234, 2016, B2,
[3] Patent: JP5819291, 2015, B2,
[4] Patent: JP2016/84297, 2016, A,
[5] Patent: US2017/273905, 2017, A1,
[6] Patent: CN105085292, 2017, B,
[7] Patent: CN105085437, 2018, B,
  • 4
  • [ 112-63-0 ]
  • [ 4102-60-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 10, p. 1183 - 1190
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